, Volume 32, Issue 4, pp 363–367 | Cite as

Nuclear magnetic resonance characterization of 6α-chloro-5β-cholestane-3β,5-diol formed from the reaction of hypochlorous acid with cholesterol

  • Anitra C. Carr
  • Christine C. Winterbourn
  • John W. Blunt
  • Andrew J. Phillips
  • Andrew D. Abell


Hyopochlorous acid generated by neutrophil myeloperoxidase has been shown to convert cholesterol into three different chlorohydrin isomers which previously had not been fully characterized. We have reacted hypochlorous acid with cholesterol/1,2-dipalmitoyl phosphatidylcholine liposomes to give these three major products and established that they are 6β-chloro-5α-cholestane-3β,5-diol (chlorohydrin 1), 5α-chloro-6β-cholestane-3β,6-diol (chlorohydrin 2) and 6α-chloro-5β-cholestane-3β,5-diol (chlorohydrin 3). These products were separated by thin-layer chromatography and fully characterized by 1H, 13C, attached proton test, doublequantum correlation spectroscopy, total correlation spectroscopy, heteronuclear multiple bond correlation and heteronuclear multiple quantum coherence nuclear magnetic resonance spectroscopy.


DPPC HOCl Hypochlorous Acid Heteronuclear Multiple Bond Correlation Chlorohydrin 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



attached proton test


1,2-dipalmitoyl phosphatidylcholine


doublequantum correlation spectroscopy


gas chromatography-mass spectrometry


heteronuclear multiple bond correlation spectroscopy


heteronuclear multiple quantum coherence spectroscopy


nuclear magnetic resonance


phosphate-buffered saline


thin-layer chromatography


total correlation spectroscopy


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Copyright information

© AOCS Press 1997

Authors and Affiliations

  • Anitra C. Carr
    • 2
  • Christine C. Winterbourn
    • 2
  • John W. Blunt
    • 1
  • Andrew J. Phillips
    • 1
  • Andrew D. Abell
    • 1
  1. 1.Department of ChemistryUniversity of CanterburyChristchurchNew Zealand
  2. 2.Department of PathologyChristchurch School of MedicineChristchurchNew Zealand

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